Halloween in Sleepy Hollow Country

If you’ve been following me for a while then you know I’m KINDA THE QUEEN OF HALLOWEEN! We’re just a few weeks away from the start Fall and that means that Halloween is right around the corner.

If you’re as Halloween obsessed as I am then you’ve definitely heard of the town of Sleepy Hollow. Located 25 miles north of New York City along the eastern shore of the Hudson River, the Village of Sleepy Hollow was immortalized in Washington Irving’s famous tale, “The Legend of Sleepy Hollow” and is now a modern village that is home to 10,000 residents.

Sleepy Hollow was given its name by its original Dutch settlers for its dreary atmosphere and supernatural occurrences surrounding witches and other ghouls. One folklore in particular – the Headless Horseman – was a Hessian solider and is a ghost without a head that rides around on horseback only at night.

FUN FACT: Sleepy Hollow is considered be some to be one of the “most haunted places in the world”, but also has been designated “the safest small ‘city’ in America”.

I think all of the above makes it pretty obvious why it’s a great idea to celebrate Halloween in Sleepy Hollow Country! Also, it’s a great destination for those who love Halloween (like me!) and as you scroll through the rest of this post you’ll see how Sleepy Hollow Country offers a wide range of Halloween events and activities for all ages.

Halloween in Sleepy Hollow Country

The Great Jack O Lantern Blaze

• One of the COOLEST Halloween experiences in the country with more than 7000 illuminated jack o’ lanterns are on display.
• The Blaze is a walk-through experience where thousands of hand carved pumpkins in elaborate displays light up the night. Includes large than life installations, along with synchronized lighting to an original soundtrack.
• Located at the historic, Van Cortlandt Manor in Croton-on-Hudson (they also have a second location now in Nassau County, Long Island at Old Bethpage Village Restoration)
• Also, it runs from September 16th – November 20th
• You can walk at your own pace and stay as long as you like, but typically it takes around 45 minutes to an hour for the entire experience.
• Advanced Tickets required!
• Moreover, all proceeds from The Blaze support the programs of Historic Hudson Valley.
• Family Friendly!
• Free parking available on site.
• 525 S Riverside, Croton-on-Hudson, NY 10520

Visit Sleepy Hollow Cemetery

• Founded in 1849, this private cemetery is 90 acres big and home to over 45,000 interments.
• Famous burials include Washington Irving, Andrew Carnegie, Walter Chrysler, Samuel Gompers, Elizabeth Arden, Leona Helmsley, Brooke Astor, and William Rockefeller. 
• So, the grounds are open daily from 8am to 4:30pm and you may walk or drive through on your own. Also, free maps, perfect for a self guided tour to major figures in the cemetery are available at both entrances.
• They also offer a variety of tours at the cemetery. (Scroll down for more info!)
• Gentle reminder to be respectful when visiting the Sleepy Hollow Cemetery – This is a private cemetery and you should act as if you are attending the funeral or grave of a beloved relative or friend. Use caution when driving and parking throughout the cemetery. They prohibit picnicking, sunbathing, littering, smoking, vaping, alcohol and drugs.
• There is a small lot to park in near the South Gate and parking is allowed along the cemetery roads. Make sure not to park on the grass or graves throughout the cemetery.
• 540 N. Broadway, Sleepy Hollow, NY 10591

Guided Tours through the Sleepy Hollow Cemetery

If you’re spending Halloween in Sleepy Hollow Country you’ll definitely want to book a cemetery tour. There are MANY different guided tours offered at the Sleepy Hollow Cemetery throughout September, October & November. Advanced tickets for all events are required and can be found HERE!

Classic Daytime Tour

• 2 hour daytime walk through the cemetery.
• Every Saturday & Sunday 2-4pm through November 27th.
• Route is approx. 1.5 miles and includes hills, stairs and unpaved roads.
• Sleepy Hollow Cemetery South Gate – 540 N. Broadway, Sleepy Hollow, NY 10591
• Free Parking!

Classic Evening Lantern Tour

• 2 hour evening tour that gives you a great overview of why Sleepy Hollow Cemetery is so famous.
• Fridays & Saturdays from 8-10pm in September. Fridays, Saturdays & Sundays in October from 7-9pm & 10pm-12am.
• Best for Ages 10+
• Route is approx. 1.5 miles and includes hills, stairs and unpaved roads.
• The Daytime & Evening Tours are the same route with the same content, they just start in a different location.
• Sleepy Hollow Cemetery North Gate – 540 N. Broadway, Sleepy Hollow, NY 10591
• Free Parking!

The Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow” Tour

• Learn all about Washington Irving and his impact on American Literature and “The Legend of Sleepy Hollow”
• 1 Hour tour exploring the South End of the cemetery.
• Route includes hills, stairs and unpaved roads.
• Saturdays & Sundays from 11am-12pm & 1-2pm through November 26th. In October this tour is offered everyday from 1-2pm.
• Sleepy Hollow Cemetery South Gate – 540 N. Broadway, Sleepy Hollow, NY 10591
• Free Parking!

American Aristocrats Tour

• 1 hour lantern tour where your meet some of the American Aristocrats, like William Rockefeller & Andrew Carnegie, who shaped our country with their ambitious visions and amassed sizable fortunes.
• Route includes hills, stairs and unpaved roads.
• Best for Ages 10+
• Friday and Saturday evening in September from 8:30-9:30pm. Daily in October from 7:30-8:30pm, also 9:30pm-10:30pm on Saturdays and Sundays in October. Select dates in November.
• Sleepy Hollow Cemetery North Gate – 540 N. Broadway, Sleepy Hollow, NY 10591
• Free Parking!

These are just a few of the many guided tours offered at the cemetery, click HERE for more including Champagne Cocktails with the Dead, Murder and Mayhem and Murder Mystery.

Eat at Horsefeathers

• While it technically isn’t one of the many historic sites in the area, if you’re visiting Sleepy Hollow during the Halloween Season (or really any time of year) you MUST eat at Horsefeathers.
• Since opening its doors in 1981, Horsefeathers has been a staple in the Westchester restaurant scene.
• Horsefeathers’ decor year round pays homage to all the spooky Sleepy Hollow fictional and non-fictional greats, like the Headless Horseman, Washington Irving, Ichabod Crane and more, but owner Julia McCue really goes all out for the month of October when it comes to Halloween decorations.
• From November to September Horsefeathers takes reservations, but during October it’s walk in only.
• Open Tuesday through Sunday for Lunch & Dinner. Saturday and Sunday they serve brunch until 2:30pm.
• 94 N Broadway, Tarrytown, NY 10591

Visit Old Dutch Church & Burying Ground

• Founded in 1685, the Old Dutch Church of Sleepy Hollow or Dutch Reformed Church is the oldest extant church in New York.
• It is featured prominently in “The Legend of Sleepy Hollow” and the burying ground is the alleged haunt of the headless horseman and resting place of local citizens who inspired Irving’s characters of Katrina Van Tassel, Brom Bones and more.
• It was designated a National Historic Landmark in 1961.
• Reminder: This is an active congregation, please be respectful of worship services, weddings and funerals.
• 430 North Broadway, Sleepy Hollow, NY 10591
• No parking on site. You must park inside the adjacent Sleepy Hollow Cemetery and walk.

Headless Horseman Bridge

• While the Headless Horseman Bridge, where the Headless Horseman hurls a pumpkin at Ichabod Crane, is one of the most sought after destinations during Halloween in Sleepy Hollow Country, it actually doesn’t exist (at least not anymore)!
• There is a rustic wooden bridge in the Cemetery that many consider the Headless Horse Bridge (and is DEFINITELY worth visiting), but its a little upstream from where the Post Road bridge stood in Irving’s time. (If you want to visit it’s just inside the cemetery’s south gate)
• There’s also a sign and bridge plaque that marks the spot of the alleged original bridge near the Old Dutch Church on a modern, concrete bridge that stretches over the Pocantico River. This is also where the statue of the Headless Horseman is located (near 362 Broadway).

Philipsburg Manor

• The 18th century plantation turned museum that includes the large stone manor house and grist mill on the banks of the Pocantico River that was home to 23 enslaved individuals. While touring the house you’ll learn about the Philipse family and the enslaved community.
• Visit here to participate in hands-on activities of the 18th century and learn the riveting yet little-known story of enslavement in the colonial north.
• Tours run from May 6-November 13th, Friday-Sunday between 10:30am & 3:30pm.
• Advanced Tickets required.
• Family friendly!
• 381 N. Broadway, Sleepy Hollow, NY 10591

Tarrytown Halloween Parade

• The 20th annual Village of Tarrytown Halloween Parade is taking place on Saturday, October 29th. It starts at 5:30pm at Patriot’s Park and runs down Broadway to Tarrytown’s Main Street.
• Block party to follow on Main Street with a DJ and live music, outdoor dining, performers and much more!
• Family Friendly!
• Viewing along the parade route is FREE!
• You can participate by marching in the parade with a theme as a group or float for a chance to win prizes! Registration is required ahead of time.

Washington Irving’s Sunnyside House

• Nestled along the banks of the Hudson River, the Landscape of Washington Irving’s Sunnyside has been charming guests for generations.
• Visitors learn about Washington Irving’s storied past and how he came to be America’s first internationally famous author. Best remembered now for The Legend of Sleepy Hollow, his characters from Brom Bones and Ichabod Crane to the Headless Horseman and the Rip Van Winkle, are American culture icons.
• From May 6-September 11 (Fridays-Sundays between 10am & 3:30pm), tours of Sunnyside are available.
• From September 16-November 13 (Fridays-Sundays, plus Columbus & Halloween) Sunnyside Home of the ‘Legend’ Tours are available. This differs from the above tour because they decorate the house for the season, there are games on the lawn and it highlights how the ‘Legend’ has lived in the imagination of popular culture for centuries.
• Advanced Tickets required.
• Parking available onsite.
• Family Friendly!
• 3 W Sunnyside Lane, Irvington, NY 10533

See Irving’s ‘Legend’ Performance

• “The Legend of Sleepy Hollow”, one of America’s first ghost stories, as you’ve never heard it before.
• Performed outdoors under the stars at Washington Irving’s Sunnyside, master storyteller Jonathan Kruk delivers a dramatic performance of the classic tale.
• Runs Fridays-Sundays plus Columbus Day & Halloween from September 30th – October 31st!
• Advance Tickets required.
• Includes live music and an appearance from the Headless Horseman himself!
• Great for all ages!
• This experience is outdoors and requires walking!
• Parking available onsite.
• 3 W Sunnyside Lane, Irvington, NY 10533

Haunted Hayride

• Follow Ichabod Crane’s flight path from the Headless Horseman down Albany Post Road past the Old Dutch Church on Sleepy Hollow’s annual Haunted Hayride.
• Stay entertained before and after your hair-raising ride at the Sleepy Hollow Block Party.
• Advanced tickets required.
• Sleepy Hollow Village Hall, 28 Beekman Ave, Sleepy Hollow, NY 10591

Sleepy Hollow Block Party

• Live music, food trucks, vendors and entertainment!
• The block party will take place on Beekman Avenue in Sleepy Hollow on the same nights that the Haunted Hayrides are running.
• October 21st & 22nd from 5pm-11pm
• Free!
• Family friendly!

Glass Pumpkin Patch

• Artist, Gregory Tomb, has partnered with the Make-A-Wish Hudson to create a Glass Pumpkin Patch in Kingsland Point Park
• The festive event will showcase over 1000 whimsical, vibrantly colored handmade glass pumpkins
• Running October 14-16th from 10am-5pm
• All proceeds support the Make-A-Wish Hudson Valley.
• Family Friendly!
• Event is FREE, but there is a fee to park.

Sleepy Hollow Lighthouse

• Also known as the Tarrytown Light, the Sleepy Hollow Lighthouse is situated just off the riverbank at the southern end of Kingsland Point Park.
• In 1979, it was listed on the National Register of Historic Places and it is the only lighthouse in Westchester County.
• Due to preservation and restoration work, the lighthouse itself is closed this season, but you can still view if from the Scenic Hudson RiverWalk.
• Kingsland Point Park, 299 Palmer Ave. Sleepy Hollow, NY 10591

Rockefeller State Park

• Donated by the Rockefeller family this park is over 1700 acres and has over 45 miles of carriage trails.
• If you’re spending Halloween in Sleepy Hollow Country then this is a great place to see the beautiful fall foliage that New York has to offer during October and go hiking, running and picnicking.
• The park is home to some of Sleepy Hollow folklore like the Spook Rock, Raven Rock and Carl’s Mill.
• Park is open year round 7am-sunset.
• Small parking fee to enter.

Hulda’s Night Event

• Hulda’s Night at Rockefeller State Park Preserve is a step back as you listen to local legends and journey up Old Gory Brook Road Trail and down Witch’s Spring Trail as you near the witch’s home (Hulda’s hut) nearby.
• Event runs October 19th-22nd & 26th-29th.
• Advanced tickets required.
• No children under 10 allowed.
• Hike is around 2 miles in length with some hills. Bring a flashlight.
• Park at 25 Sleepy Hollow Rd., Sleepy Hollow, NY 10591

Armour-Stiner (Octagon) House

• The Armour Stiner House is an octagon-shaped and domed Victorian-style house.
• It is the only known fully domed octagonal residence and the only house which replicates Donato Bramante’s 1502 Tempietto in Rome.
• It was designated a National Historic Landmark in 1976.
• The Octagon House is a private family home and access to the house and the grounds is only available to ticket holders.
• The Octagon House offers a classic tour from April to December along with many seasonal tours including their Fall/Halloween Tour during the months of September and October.
• This year, “Myths and Mysteries of The Octagon House” is a tour that focuses on supernatural myths and mysteries about the house.
• Parking is very limited!
• Best for ages 12 and up!
• 45 W Clinton Ave, Irvington, NY 10533

Tarrytown Music Hall

• The Music Hall was built in 1885 during the Millionaire’s Colony Era when mansions dotted the Hudson Valley landscape and families such as the Rockefellers, Goulds and Vanderbilts gathered at the Music Hall to participate in its lavish balls, flower shows and concerts.
• Unexplained happenings and paranormal activity have been experienced at Tarrytown Music Hall. Lights mysteriously turn back on after closing, the eerie sound of an unknown singer performing vocal scales in the wings after hours and more. Some artists have ever refused to stay in one particular dressing room because they “sensed a presence”.
• 2022 Ghost Tours to be announced soon.
• 13 Main St., Tarrytown, NY 10591

Kykuit

• Kykuit, The Rockefeller Estate is a majestic paradise with sweeping river views. It was home to John D. Rockefeller, founder of Standard Oil, the richest man in America at his time and not it’s a historic site that has been meticulously maintained for more than 100 years.
• Tours run Saturday & Sunday from May 21st-October 2nd. Wednesday-Monday between October 5th-November 13th.
• All guided tours start from the Visitor Center at Philipsburg Manor at 381 North Broadway, Sleepy Hollow, NY and include a shuttle bus ride to the estate.
• Advanced tickets required.

Horseman’s Hollow

• Unfortunately it’s not running this year, but hopefully it’ll be back next year.

PIN my Halloween in Sleepy Hollow Country Post for LATER:

Looking for more Halloween inspiration? Check out my Halloween page!

& check out my Halloween loving friends featured here too! Simone, Tiffany, Julia & Riley!